Holiday Rentals in Darlington

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Our top choices for Darlington holiday rentals

Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (48)
"It was a great place to stay!!! The owners were great to deal with!!! Will be coming back"
United States
Michelle M.
The price is €198
includes taxes & fees
31 Dec - 1 Jan 2026
Hamilton Goebel House 816 E Louisa St Darlington Wi

Lovely 3-bedroom house with WiFi in Darlington

Lovely 3-bedroom house with WiFi in Darlington
Darlington
2.0 out of 10, (1)
"This property was under construction still and the property manager was out of town and unreachable."
United States
Melissa S.
The price is €191
includes taxes & fees
30 Dec - 31 Dec
Lovely 3-bedroom house with WiFi in Darlington

Sugar River Suite - Your Sweet Escape in the Heart of it All!

Sugar River Suite - Your Sweet Escape in the Heart of it All!
New Glarus
10.0 out of 10, Exceptional, (20)
"Super clean & right in the middle of town. Great place for a girls getaway weekend!"
United States
Rachel I.
The price is €156
includes taxes & fees
2 Jan - 3 Jan 2026
Sugar River Suite - Your Sweet Escape in the Heart of it All!

Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm
Lena
10.0 out of 10, Exceptional, (12)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is €148
includes taxes & fees
2 Jan - 3 Jan 2026
Peace & Simplicity in a Little Red Cabin on the Farm

Beautiful two story, downtown home, one block from the Square,

Beautiful two story, downtown home, one block from the Square,
Monroe
10.0 out of 10, Exceptional, (35)
"The property was wonderful and the hosts were great/accommodating. Wonderfully decorated, charming and location was perfect (as we were looking to be near the square for bars, restaurants and shopping).Highly recommend!"
United States
Frank B.
The price is €248
includes taxes & fees
8 Jan - 9 Jan 2026
Beautiful two story, downtown home, one block from the Square,

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (119)
"Great location two blocks off main street. Really neat old house with everything you need, we would definitely stay again!!"
United States
Jeff B.
The price is €216
includes taxes & fees
29 Dec - 30 Dec
A Comfy Cozy Cottage on Clowney

MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (102)
"Such a fun place to stay! We loved it!"
United States
Karen J.
The price is €229
includes taxes & fees
4 Jan - 5 Jan 2026
MJ's Penthouse ,a piece of paradise on Monroe's historic square

Close to Local Opera House - On the main drag

Close to Local Opera House - On the main drag
Downtown Mineral Point
9.8 out of 10, Exceptional, (42)
"Perfect located close to Opera House "
United States
B C.
The price is €154
includes taxes & fees
16 Jan - 17 Jan 2026
Close to Local Opera House - On the main drag

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
2.0 star property
Monroe
The price is €185
includes taxes & fees
5 Jan - 6 Jan 2026
Lookout Loft over the Monroe Square

Scenic Getaway – Cozy Stay Near Golf & Trails

Scenic Getaway – Cozy Stay Near Golf & Trails
The Galena Territory
10.0 out of 10, Exceptional, (70)
"We love the Galena Territory. "
United States
Eric T.
The price is €241
includes taxes & fees
26 Jan - 27 Jan 2026
Scenic Getaway – Cozy Stay Near Golf & Trails

Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (106)
"Outstanding property, great location, will stay again."
United States
James S.
The price is €180
includes taxes & fees
29 Dec - 30 Dec
Serenity Cottage at Mineral Point

Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point

Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point
Dodgeville
9.2 out of 10, Wonderful, (13)
"Check in and host were awesome. Very peaceful and relaxing"
United States
Theresa H.
The price is €255
includes taxes & fees
31 Dec - 1 Jan 2026
Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point

Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View

Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
The Galena Territory
10.0 out of 10, Exceptional, (41)
"Everything was great! Beautiful place, close to town and very quiet."
United States
Lori
The price is €232
includes taxes & fees
5 Jan - 6 Jan 2026
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View

Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena

Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
The Galena Territory
9.8 out of 10, Exceptional, (26)
"Everything was so smooth and so great!!! Loved it and can’t wait to come back!"
United States
Nicholle H.
The price is €253
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena

Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!

Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!
The Galena Territory
10.0 out of 10, Exceptional, (53)
"Golf View is a lovely townhouse, bright, very clean, fun/well appointed decor & easy to access. "
United States
Diane
The price is €232
includes taxes & fees
28 Jan - 29 Jan 2026
Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Elizabeth
10.0 out of 10, Exceptional, (4)
"We had 14 people stay for a business retreat. Each had their own bedroom and bathroom. We gathered in the great room for our meeting, experienced cooking together and a ‘family dinner’ around the big table. We hiked as our activity and enjoyed a bonfire too. We went into galena one evening for dinner - just a quick 20 minute drive. We enjoyed our short stay and would consider returning."
United States
Katie L.
The price is €5,444
includes taxes & fees
5 Jan - 6 Jan 2026
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

Private 3BR/2BA Territory Home Nestled in the Trees

Private 3BR/2BA Territory Home Nestled in the Trees
The Galena Territory
10.0 out of 10, Exceptional, (137)
"The property was beautiful, clean and within a 12 minute ride from Galena."
United States
Ellen S.
The price is €249
includes taxes & fees
7 Jan - 8 Jan 2026
Private 3BR/2BA Territory Home Nestled in the Trees

Winter Escape in Galena - Wood-Burning Fireplace, Pool Access, 2 King Beds, Ski

Winter Escape in Galena - Wood-Burning Fireplace, Pool Access, 2 King Beds, Ski
The Galena Territory
10.0 out of 10, Exceptional, (75)
"Melissa's place was perfect for our girls' weekend. Super clean, well-stocked kitchen, and even a thoughtful note & snacks upon arrival. It's in a great golf community with wonderful amenities. Would definitely stay here again!"
United States
Kathryn P.
The price is €214
includes taxes & fees
13 Jan - 14 Jan 2026
Winter Escape in Galena - Wood-Burning Fireplace, Pool Access, 2 King Beds, Ski

“Steps into Little Switzerland” Indoor Parking at The Belvedere.

“Steps into Little Switzerland” Indoor Parking at The Belvedere.
New Glarus
10.0 out of 10, Exceptional, (7)
"LOVELY PLACE! 3 comfy beds, nice bathrooms, living toom & large dining table easily accommodated our group. The kitchen was well stocked for us to prepare our meals. Great location, easy walking around the fun town!!"
United States
Brooke
The price is €597
includes taxes & fees
17 Jan - 18 Jan 2026
“Steps into Little Switzerland” Indoor Parking at The Belvedere.

Home away from home right off the trail between Mineral Point and Darlington

Home away from home right off the trail between Mineral Point and Darlington
2.0 star property
Mineral Point
10.0 out of 10, Exceptional, (3)
"It was a very lovely house and host. Perfect for the trail, and could easily accommodate a large family."
United States
amber s.
The price is €191
includes taxes & fees
5 Jan - 6 Jan 2026
Home away from home right off the trail between Mineral Point and Darlington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Darlington Hotel Reviews

Find out more about Darlington

Everything you need to know about Darlington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Darlington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darlington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Darlington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darlington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Darlington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darlington holiday rentals we have selected for you start as low as €201 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Darlington rentals

At Expedia, we put the best Darlington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Darlington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darlington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darlington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Darlington?

Yes, there are holiday rentals close to the most popular sights in Darlington, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Darlington has a good selection of restaurants. Make sure you have time to check out the architecture and coffee shops during your trip.

What are some of the best holiday rentals that Darlington has to offer?

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.: This holiday home rental outside of Darlington is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Darlington?

Expedia has 7 holiday rentals for your stay in Darlington.

What’s there to see and do in Darlington?

Explore the area and family-friendly sights such as Roelli Cheese Haus, or get out into nature at a spot like Yellowstone Lake State Park. Lamont Town Hall and Yellowstone State Wildlife Area are other places to visit while you're in town.

What’s a holiday rental in Darlington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Darlington. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.